Synthesis of Biaryl Carboxylic Acids through a Cascade Suzuki-Miyaura Coupling/Friedel-Crafts Alkylation/Lewis-Acid-Catalyzed Rearrangement/Aromatization Process
In this study, we present a series of 1,3-dicarbonyls that can undergo a cascade Suzuki coupling, followed by a Friedel-Crafts reaction to produce molecules containing polycyclic alcohols. These polycyclic alcohols can then be converted into biaryl carboxylic acids through ring-opening rearrangement reactions catalyzed by a Lewis acid. The Friedel-Crafts reaction exhibits selective para-positioning of the hydroxyl group and demonstrates good compatibility with functional groups with a yield of up to 82%. Substrates with substituted hydroxyl groups can also be converted into biaryl carboxylic acids through a Lewis-acid-catalyzed ring-opening rearrangement.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Organic letters - 26(2024), 9 vom: 08. März, Seite 1902-1907 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Liu, Shaodong [VerfasserIn] |
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| Anmerkungen: |
Date Revised 08.03.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.4c00204 |
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NLM369110757 |
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| 245 | 1 | 0 | |a Synthesis of Biaryl Carboxylic Acids through a Cascade Suzuki-Miyaura Coupling/Friedel-Crafts Alkylation/Lewis-Acid-Catalyzed Rearrangement/Aromatization Process |
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| 500 | |a Date Revised 08.03.2024 | ||
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a In this study, we present a series of 1,3-dicarbonyls that can undergo a cascade Suzuki coupling, followed by a Friedel-Crafts reaction to produce molecules containing polycyclic alcohols. These polycyclic alcohols can then be converted into biaryl carboxylic acids through ring-opening rearrangement reactions catalyzed by a Lewis acid. The Friedel-Crafts reaction exhibits selective para-positioning of the hydroxyl group and demonstrates good compatibility with functional groups with a yield of up to 82%. Substrates with substituted hydroxyl groups can also be converted into biaryl carboxylic acids through a Lewis-acid-catalyzed ring-opening rearrangement | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Liu, Li |e verfasserin |4 aut | |
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